Principal Product Manager

About the role

This role is for Principal Product Managers who are builder-minded and deeply curious about how AI can meaningfully transform mental healthcare delivery rather than treating it as a superficial feature. You will own a significant product domain from end to end, defining strategy, aligning stakeholders up to and including executive leadership, and establishing a high benchmark for what great product execution looks like within the Headway ecosystem. The best candidates bring a track record of identifying the right problems and persuading the organization to solve them, even when the path forward is ambiguous and the stakes are high. You will work with a high degree of autonomy on problems that do not have immediately obvious answers, shaping the roadmap from first principles instead of merely executing on a plan handed from above. This is a role for builders who are equally comfortable wrestling with nuanced human needs, complex clinical realities, and sophisticated technical systems to drive durable impact in mental healthcare.

Key facts

What you'll do

• Define the strategy for a major product domain and identify the highest-leverage bets Headway should pursue, making the case with data, customer insight, and clinical context while driving alignment across engineering, design, clinical, legal, operations, and executive leadership.
• Ship meaningful product that delivers measurable outcomes, owning the roadmap end-to-end, navigating tradeoffs under uncertainty, and maintaining a high bar for quality, reliability, and velocity in production.
• Build long-term foundations by creating capabilities, frameworks, and systems that unlock multiple years of product work across your domain, rather than focusing exclusively on short-term deliverables.
• Elevate the craft of product management on your team by setting the standard for rigorous thinking, mentoring other PMs, raising the hiring bar, and influencing how the broader product organization operates and collaborates.
• Drive alignment across complexity without formal authority, working closely with engineering, design, data, clinical, legal, operations, and finance partners to translate ambiguous problems into coherent product solutions.
• Partner with data and analytics to define meaningful success metrics, design rigorous evaluation approaches, and use insights to iterate quickly while building confidence that the product is moving meaningful outcomes for patients, providers, and payers.
• Collaborate with clinical and compliance experts to ensure that AI-powered features, workflows, and automation meet the realities of mental healthcare delivery, uphold ethical standards, and support safe, effective care.
• Own the end-user experience for critical workflows, balancing the needs of patients, providers, and payers, and making thoughtful tradeoffs that preserve clarity, trust, and usability even as the product grows in scope.
• Translate complex stakeholder perspectives into a clear product narrative that resonates across the organization, aligning teams on priorities and building sustained momentum behind difficult bets.
• Explore how AI can automate and improve clinical workflows, simplify insurance and credentialing processes, and support providers in running thriving practices with less administrative burden.
• Measure and communicate the impact of product initiatives on key stakeholders, including patient access, provider efficiency, payer outcomes, and platform reliability, using both qualitative and quantitative evidence.
• Partner with platform and infrastructure teams to ensure that product initiatives scale reliably, leveraging AI to automate high-volume operational tasks, strengthen trust and safety, and improve system performance.
• Work with data and experimentation teams to design tests that clarify causality, surface edge cases, and validate assumptions, ensuring product decisions are grounded in evidence rather than intuition.
• Represent Headway in external conversations and partnerships where appropriate, gathering insights that inform product direction and strengthening the company's relationships with key stakeholders in the mental health ecosystem.

Requirements

You have at least 8 years of experience in product management, with a significant portion of that time spent in a senior or principal role owning complex domains. You hold a Bachelor's degree or equivalent practical experience, and you bring 8+ years of hands-on experience managing the full product lifecycle in a fast-paced, data-informed environment. You are comfortable making decisions in situations with incomplete information and have a proven ability to define problems, set strategy, and rally cross-functional teams around ambitious goals. You communicate clearly and persuasively with executives, practitioners, and engineers, adapting your style and depth of detail to your audience while maintaining a strong bias for action. You are fluent in core product management practices, including roadmapping, prioritization, metrics design, stakeholder management, and scoping, and you use these tools to drive outcomes in ambiguous, dynamic contexts. You understand how to partner with data, analytics, and research teams to surface insights, validate hypotheses, and build confidence in product decisions over time. You have experience working with regulated environments and complex operational workflows, and you appreciate the importance of compliance, security, and reliability in building products that people depend on.

Nice to have

Experience working in mental healthcare, insurance, or highly regulated industries is preferred, as is familiarity with AI tools and workflows in a product role. Background in clinical operations, therapy delivery, or payer-provider relationships would be especially valuable, along with prior experience leveraging data and experimentation to drive product decisions in complex environments.

Practical notes

This role is full-time and remote.